


There's Always a First

by WhatSaidWho (Wildhero)



Category: Once Upon a Time (TV)
Genre: Angst with a Happy Ending, F/M, First Time, Light Angst, Loss of Virginity, Virginity
Language: English
Status: In-Progress
Published: 2017-07-21
Updated: 2017-07-21
Packaged: 2018-12-05 15:59:59
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,682
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11581383
Author URL: https://archiveofourown.org/users/Wildhero/pseuds/WhatSaidWho
Summary: Killian reveals big news to Emma.





	1. Chapter 1

**Author's Note:**

> I've seen a lot of first time fics in this fandom, but not much for loss of virginity and definitely not for a canonical version where Killian is the virgin! Thought I would try to add some more diversity. Virgin!Killian  
> There will be more chapters. I will try to upload a new one every one to two days for right now until they start getting longer. Right now it's more of an idea jotted down. Not beta'd.  
> I only own the idea, not the characters or show.

       It was a quiet day which was a such a rarity in Storybrooke that Emma was sure something was about to happen, but that didn’t stop her from taking advantage of it. And what better way to take advantage of it than making out with her pirate boyfriend in their newly acquired house. Their house. Emma quite liked the sound of that.  
Falling back onto the couch, remaining lip locked with Killian, Emma began to smile causing Killian to smile too.

       “What are you thinking about, luv?” Killian asked in between kisses.

       “Nothing, just kiss me.”

       Not needing to be told twice, Killian resumed kissing Emma fervently. It wasn’t long before they were both gasping for breath and letting out quiet, involuntary moans. Emma quickly started working the buttons on Killian’s vest, groaning when she couldn’t get them undone fast enough.

       “Slow down, darling,” Killian whispered against her lips as he pushed her hands away lightly. “All in due time, I promise.”

       “Screw ‘due time’. I want you,” she stated bluntly as she wrapped her legs around his hips and ground against his ever-present arousal. “And don’t try to tell me you don’t want me too.”

       “I do, luv. Of course I do. But it’s not that simple.”

       Frustrated, Emma lets out a huff of air and swings her legs off of him and sit up, righting her clothes. “Look, Killian. I’m not a teenager. You don’t have to give me excuses. Clearly you don’t want to sleep with me.”

       As Killian moves to sit by her, he runs his hand through his hair roughly, messing it more than Emma had already. “Why would you think I wouldn’t want to sleep with you, Emma? You’re a bloody siren. I want nothing more than to lay you down and make you feel as amazing as you are.”

       Emma released a weak laugh before finally turning her gaze off the floor towards Killian. “Why would I think that? Oh, I dunno, Hook. Maybe because we’ve been together for three months now and every time I go to take it further than some light petting, you turn me down.”

       Sighing, Killian grabs Emma’s hand and places a featherlight kiss on her knuckles, buying himself some time to prepare for the conversation he knows he can no longer run away from. “Emma, my love, I promise that that has nothing to do with you. I want you more than you could ever possibly imagine. You are the most beautiful woman this pirate has ever laid eyes on and you deserve to have someone bring you pleasure—“

       “Then why don’t you?” Emma interrupted.

       “Because, I’m afraid I haven’t been entirely honest with you.” Emma’s gaze turned curious at Killian’s statement and she glanced very quickly down at Killian’s crotch before glancing back up. With a light hearted laugh, Killian continues, “I guarantee you, princess, everything works quite fine. It isn’t that. It’s…well, you see, it’s…” Killian drifts off.

       Giving Killian’s hand a light squeeze, Emma gives a reassuring nod, asking for an explanation without words.

       With a deep breath, Killian blurts out, “Well, Swan, I’m a virgin.”


	2. Chapter 2

**Notes for the Chapter:**

> Hey, guys. An update as promised. I'm thinking this one may be a short fic. Maybe only four-five chapters. Could definitely see turning it into a series type thing though, so let me know if you'd be interested in that. I do know where this is heading so updates should be pretty quick, but the chapters are getting progressively longer so you win some you lose some. 
> 
> I only own the idea, not the show or characters or anything that's familiar to you.

       After what seems to be forever in Killian’s eyes, Emma starts laughing.

      “No, come on, Killian. Seriously, why won’t you sleep with me?” she asks.

       Embarrassed and confused, Killian quickly becomes defensive.

       “Look, Swan, if you are just going to laugh at me, I’m going to leave to save what very little of my dignity I have left.”

       Killian stands from the couch before Emma grabs his arm to anchor him here and she stands, suddenly serious.

       Quietly, barely above a whisper she asks, “Killian, you’re not kidding?”

       “Pray tell, Emma. Where is the joke in all of this?” Killian probes bitterly.

       Emma stands there wide eyed but her voice low and steady.

       “How? How can you be a virgin? You’re three hundred and some years old. You boast all the time of the bar wenches and—and what about Milah? You mean to tell me you’ve never had sex? I just—I don’t understand. I don’t believe it.”  
 

      Killian’s cheeks flush under the scrutiny of Emma’s gaze before responding, “Can’t you just take me for my word and carry on now that you know?

       Emma sits back down and motions for him to do the same, waiting for him to sit before answering.

       “Don’t you think this needs a little more conversation? I’m still having a hard time believing I’m not being Punk’d or something,” Emma pauses at Killian’s confused look, “It’s a tv show ab—You know, not really relevant. Just,” moving her hand down to his hand, she rubs her thumb comfortingly over the back of it, “Talk to me.”

       After a deep breath that steadied Killian, he looked at Emma and tried to bare everything just through his eyes, allowing her to see his sincerity.

       “Well, Swan, okay. If you think we really need to talk about this—“

       “We do.” She interrupted.

       “—Then we will. What do you want to know? I’m just shy of three hundred, yes. The bar wenches were in fact real, but I never slept with them. I made it appear as if I did for the sake of appearances with my crew, but I would simply pay them and make them wait to leave. Milah was, well, let’s just say that she had had enough after her pregnancy. She didn’t desire it. Swan, I’m an honest man. Take me at my word when I tell you, no, I have never had sex.”

       Emma stared, slack jawed at his confession. She had assumed that their lack of intimacy came from a constant crisis. Not from his lack or prowess. “Why?” she asked, quietly and curiously. No judgement present in her voice.

       “As you said yourself, I am an old man. I was raised in a different era. In the Enchanted Forest, of course there was intercourse out of wedlock, but I was raised to be a gentleman and my mother sat my brother and I down one night when we were but lads after my poor excuse of a father came home piss drunk and she explained how a gentleman must act. One of those things was to never bed a woman unless you have every intention of making her your wife.” He hid his eyes from Emma, whether in embarrassment or shame she wasn’t sure. “Luv, I know you’re not one for roots. That’s why I haven’t shared this with you before. I do want you, but my mother was the light in my childhood and I refuse to tarnish her name by not valuing the lessons she preached to me.”

       Removing her hand from his, Emma sits quiet reflecting on what he shared with her.

       “So, you’re one of those ‘no sex until you’re married’ kind of guys, huh?”

       “Not quite. No sex until I’m positive I’m with the woman I want to be with forever.”

      “Killian, I—”

       “I know it’s too fast. I apologize for bringing it up, luv. I just thought you should know.”

       “Killian, you said you wanted to ‘carry on’.” Emma states sort of breathlessly.

       “Aye, I did.”

       “You know, we don’t have to—”

       “Darling, I want to,” he protests, looking her straight in the eye.

       “But you just said…”

       “I’m aware of what I just said,” he smiles at her shyly. 

       “So does that mean…?”

       “Aye, luv.”

       Emma moves to stand up and Killian wraps his hand around her wrist, positions reversed from earlier. “I know that commitment scares you, Swan, and do not try to act as though it doesn’t. This is in no way a proposal or am I asking you for reciprocity in your feelings for me. All this means is that- as I told you before- I will never stop working to earn your heart.”

       Killian thinks he sees some moisture in her eyes before she pulls herself away from his grasp and leaves the room. Angry at himself, he picks a throw pillow off of the ground and throws it at the wall, but the full thump that came from the contact did nothing to ease his mind. He reaches inside of his boot and wraps his fingers around the metal flask he keeps there and after a while, the hot burn that the rum provided was almost enough to make him forget why he was drinking at all.

 

**Notes for the Chapter:**

> Please comment to let me know what I did wrong. Looking for a friend who likes to beta.


	3. Chapter 3

**Notes for the Chapter:**

> HEY I'M BACK! I didn't desert you, I swear. College started and really kicked me on my ass. But I saw a cute prompt the other day and I wrote a quick oneshot for Captain Swan about it and that made me want to come back here and finish this one. I have this chapter here and I am working on the next one and I think that will be it. The next chapter will contain smutty goodness. Enjoy!

              It technically isn’t until the next day that Killian sees Emma again. It’s five in the morning when Emma quietly sneaks back in and Killian is passed out on the bed in their room with an empty bottle of Jack on the floor. She feels a twinge of guilt pass through her gut when she sees how she destroyed this man. This is the man that would- and has- die for her, but for some reason hearing him say it out loud that he was planning on being here to stay was too much for her to handle.

              She walked over to the en suite and quickly changed into clothes more comfortable than a leather jacket and jeans to sleep in. Standing in the doorway, she took the time to just stop and really look at Killian.

              She knew he was handsome. Hell, a blind gay nun would know that this man was handsome. But it wasn’t that. He was _beautiful_. All the trauma that this man had gone through and yet he’s willing to put himself on the line _again_. For _her_. Every time he got broken, it seemed he’d stood back up to make sure it wouldn’t happen to anyone else.

              Under it all, Emma is only a human. Of course, she fell for the charm, wit, and looks, but the completely unconditional love made it hard. How can she explain that she wants it _so_ badly, but it suffocates her as well? She was never upset after his confession, but it broke her heart that here was this perfect example of a man who has waited for almost three hundred years for something that she took advantage of as soon as she can. He’s willing to give her everything he has—emotionally and physically—and she has nothing to give in return. She’s a wilted flower, but for some reason, he’s picked her.

              Emma walked over to the medicine cabinet in the en suite and grabbed some ibuprofen and poured a cup of water and sat it on the nightstand by the bed before righting his position (or at least trying—he’s not exactly a feather pillow here) and settling into bed with him.

              But, try as she may, she simply could not sleep. Her thoughts were plaguing her. So she did all she could think of. She wrote a note.

              Killian was always up before her anyways. Something about a sailor rising with the sun, hangover and all. So maybe they could save some time and she could explain herself in the note.

>               _Killian,_
> 
> _Take the pills and drink the water. I know that you’re well accustomed to hangovers, but these will help, trust me. Now that that’s out of the way-_
> 
> _First, I did not leave last night because of you, so I’m afraid you wasted all that liquor for nothing, Captain. Bad form wasting liquor. I left last night because I’m afraid that I don’t deserve you. You spent years refraining from something in order to make it more meaningful and I jumped in the back of a stolen car with the car thief when I was eighteen. You deserve someone who can share the experience with you. As you can see, this isn’t a goodbye letter. I’m not going anywhere. Fuck I’m bad at letters. My point was just- you said you would never stop working to earn my heart. It’s already yours, Killian. I’m here in whatever way you’ll have me._
> 
> _~Emma_

_(P.S. Commitment isn’t as bad as it seems…)_

              Before she could second guess herself, she put the note next to the water and ibuprofen, turned out the light, and fell asleep.

              Sure enough, Killian woke up the next morning with the sun and a headache, but it wasn’t the worst he’s had and within a few hours, he’ll be good as new. It wasn’t the first thing on his mind though. Though the exact actions of the previous night weren’t as vivid as the may have been, he remembered Emma leaving, but sure enough, here she was in their bed with him. In a tank top. And that scrap of fabric that she dares call “shorts”. And no bra. Bloody buggering hell.

              Closing his eyes and taking a deep breath to calm himself as he does every morning, he turns on his side to check the time on the really rather convenient number box—clock—when he noticed some out of place items. The first thing he paid any attention to was the water. He downed the bottle and then noticed the pills laying there. Surely his Swan laid them out for him so they must bear some medicinal qualities, but he decided to make use of the note lying on the stand before he went any further. After all, Swan was quite mad last night. Perhaps, they would turn him to a mouse. Seemed unlikely but, as the saying goes, Hell hath no fury.

              So he opens the piece of paper and reads.

>               _Killian,_
> 
> _Take the pills and drink the water. I know that you’re well accustomed to hangovers, but these will help, trust me._

              Well, he thought as he swallowed the pills, at least she thought about me. Even if I was a blithering idiot that went out and got drunk in the first place so that she had to take care of me.

> _First, I did not leave last night because of you, so I’m afraid you wasted all that liquor for nothing, Captain. Bad form wasting liquor._

He laughed. He knew she was stalling, but the comedic relief was not unwelcome. He read on.

> _I left last night because I’m afraid that I don’t deserve you. You spent years refraining from something in order to make it more meaningful and I jumped in the back of a stolen car with the car thief when I was eighteen. You deserve someone who can share the experience with you._

              Oh, Gods. He’d hoped that she wasn’t going where he thought she was. But no, she was in their bed. Killian shook his head pitifully. That’s not why he said it. Not to make her feel less than.

> _As you can see, this isn’t a goodbye letter. I’m not going anywhere. Fuck I’m bad at letters._

              He barked a quiet laugh of relief.

> _My point was just- you said you would never stop working to earn my heart. It’s already yours, Killian. I’m here in whatever way you’ll have me._
> 
> _~Emma_
> 
> _(P.S. Commitment isn’t as bad as it seems…)_

              Killian was completely speechless (which was a rare thing). Not only had she just admitted that he held her heart, but she also alluded that she may be on board with “forever”.

              Overcome with joy, Killian turned around to speak with Emma to find her still blissfully asleep. Between the gentle light the sun provided through the curtains and her own natural beauty, Killian was awestruck by her. He decided that he wanted this more than anything he’s ever wanted.

              He leant over to place a gentle kiss on her lips. She didn’t stir. In fact, it wasn’t until he moved his hand up on her thigh to brace himself and kiss her a little harder that he got a reaction. A moan. Albeit a quiet one, it was a moan nonetheless. Killian made a promise to himself right then. He would make this woman feel more pleasure than she ever has in her life. Sensing her becoming more conscious, he moved his hand up on the side of her breast and moved his mouth down her neck to suck at her pulse point there.

              Emma woke up.  

**Notes for the Chapter:**

> If you like my writing, lemme know.  
> If you hate my writing, lemme know.  
> If you have a prompt for me, lemme know.  
> If you have a request for me, lemme know.
> 
> In short, lemme know.

**Author's Note:**

> Please, feel free to comment. I definitely need criticism. This is my first fic and I just really wanted to get the ball rolling. If you like the prompt, message me and let me know so I can read it but feel free to use it to make it your own story.  
> Also, I am looking for a beta for this story. Let me know if you are interested.


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